5,7-Diacetyl-13-benzyl-7,8-dihydro-5H,8aH,13H-di­indolo[2,3-c;2,3-d]pyrimidin-8-yl acetate, the result of an intra­molecular cyclo­addition between an N-benzyl­indole and a 1,2,4,5-tetra­zine

✍ Scribed by Helliwell, Madeleine ;Corden, Steven ;Joule, John A.

• Publisher: International Union of Crystallography
• Year: 2007
• Tongue: English
• Weight: 339 KB
• Volume: 63
• Category: Article
• ISSN: 1600-5368
• DOI: 10.1107/s1600536807011166

✦ Synopsis

An intramolecular Diels-Alder-type cycloaddition between an indole and a 1,2,4,5-tetrazine produced the title compound, C 29 H 26 N 4 O 4 , the first example of a pentaheterocyclic structure obtained via loss of nitrogen and addition of the elements of acetic anhydride. Of the four N atoms in the molecule, one is in a dihydroindole, while the other three are in an N,N 0diacylamidrazone unit, of which there are no previous examples. The N,N 0 -diacylamidrazone is almost planar and is involved instacking with the N-benzyl phenyl ring. There are intermolecular C-HÁ Á ÁO hydrogen bonds, linking the molecules into chains.